Your best bet for entertainment is at the Mount Irvine Bay Hotel at Mount Irvine Bay (tel. 868/639-8871), where you might find some dance action or a steel band performing by the beach or pool.
Grafton Beach Resort at Black Rock owns one of the island's most charming bars, Buccaneer's Beach Bar (tel. 868/639-0191), across from the resort. Here you'll find a wide wood terrace sheltered by a grove of almond trees. Daily specials written up on a surfboard include burgers, fried fish, and the like (don't expect the elegant beachside Creole cooking of Martinique). The resort itself offers cabaret-like entertainment nightly. Try to catch the local troupe, Les Couteaux Cultural Group, which performs a version of Tobagonian history set to dance.
Want some local action? Try Bonkers, Store Bay Road at Crown Point (tel. 868/639-7173), a lively bar where you'll hear the best soca, reggae, or jazz on the island. If you've been "bad," the DJ might order you to walk the gangplank into the pool.